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AI Transformation Lead

New York, NYRemote7+ YOE
Summary

Strategic customer-facing role driving large-scale AI workflow adoption for enterprise fashion and retail brands. Partners with design, merchandising, and executive teams to implement AI transformation initiatives.

About the role

Responsibilities

  • Become a deep expert in Raspberry AI’s platform, workflows, and evolving capabilities across design, merchandising, and product development use cases.
  • Partner closely with enterprise customers to understand how teams adopt and operationalize AI across creative and production workflows.
  • Identify high-performing customer workflows and translate them into scalable playbooks, implementation strategies, and best practices for broader customer adoption.
  • Advise customers on organizational and operational changes required to successfully implement AI workflows across large teams and cross-functional organizations.
  • Drive AI transformation initiatives across enterprise retail organizations ranging from hundreds to thousands of users.
  • Work cross-functionally with Product, Engineering, Customer Success, and Sales teams to influence product direction and improve customer outcomes.
  • Create clear documentation, enablement materials, workflow frameworks, and executive-ready recommendations for internal and external stakeholders.
  • Lead strategic customer workshops, product trainings, workflow audits, and executive business reviews.
  • Act as a trusted advisor to customer leadership teams, helping them understand how generative AI can improve speed, efficiency, creativity, and organizational alignment.
  • Surface recurring workflow gaps, customer pain points, and operational insights to influence roadmap prioritization and product strategy.
  • Stay at the forefront of AI-native creative workflows and emerging industry trends across fashion, retail, and digital product creation.

Requirements

  • 7+ years of experience in fashion technology, enterprise SaaS, AI workflow consulting, product operations, digital transformation, or creative systems implementation.
  • Deep understanding of retail, fashion, or product development workflows across design, merchandising, sourcing, and production organizations.
  • Strong familiarity with generative AI tools and creative workflows using platforms such as Midjourney, Firefly, ComfyUI, Krea, Runway, or similar systems.
  • Experience driving operational change management or technology transformation initiatives within large organizations.
  • Exceptional communication and storytelling skills — able to influence both executive stakeholders and hands-on creative teams.
  • Proven ability to translate complex product capabilities into practical operational workflows and measurable business outcomes.
  • Highly strategic and systems-oriented thinker who can connect individual workflows to broader organizational transformation.
  • Strong documentation and enablement skills with the ability to create scalable frameworks, playbooks, and customer education materials.
  • Comfortable navigating ambiguity and operating in fast-moving, high-growth environments.
  • Strong cross-functional instincts with experience partnering across Product, Engineering, Customer Success, and GTM teams.
  • Passion for AI-native workflows and excitement about shaping the future of fashion and retail technology.
  • Self-starter mentality with a high level of ownership, accountability, and operational rigor.
Skills
Generative AIMidjourneyFireflyComfyUIKreaRunwayChange ManagementWorkflow DesignEnterprise SaaSProduct OperationsDigital TransformationCross-functional Collaboration